The present invention relates to dihalopropene compounds, insecticidal/acaricidal agents containing these compounds as active ingredients, and intermediates for their production.
As disclosed in JP-A 48-86835/1973 and JP-A 49-1526/1974, for example, it is well known that some kinds of propene compounds can be used as an active ingredient of insecticides.
In view of their insecticidal/acaricidal activity, it cannot always be said that these compounds are satisfactorily effective for the control of noxious insects, mites and ticks.
The present inventors have intensively studied to find a compound having excellent insecticidal/acaricidal activity. As a result, they have found that particular dihalopropene compounds have satisfactory insecticidal/acaricidal activity for the control of noxious insects, mites and ticks, thereby completing the present invention.
That is, the present invention provides a dihalopropene compound (hereinafter referred to as the present compound) of the general formula: 
wherein Z is oxygen, sulfur or NR4 (wherein R4 is hydrogen or C1-C3 alkyl); Y is oxygen, sulfur or NH; X""s are independently chlorine or bromine; R2, R3 and R10 are independently halogen, C1-C3 haloalkyl or C1-C3 alkyl; t is an integer of 0 to 2; and R1 is Q1, Q2, Q3, Q4, Q5, Q6 or Q7 of the general formula: 
wherein A is an optionally substituted heterocyclic ring group, provided that when A is an optionally substituted heterocyclic ring group containing two oxygen atoms and a condensed benzene ring, A is optionally substituted 1,3-benzodioxolan-2-yl or optionally substituted 1,4-benzodioxan-2-yl; B is oxygen, S(O)q, NR9, C(xe2x95x90G1)G2 or G1C(xe2x95x90G2); q is an integer of 0 to 2; R9 is hydrogen, acetyl or C1-C3 alkyl; G1 and G2 are independently oxygen or sulfur; R5, R6, R11 and R12 are independently hydrogen, C1-C3 alkyl or trifluoromethyl; R13 and R14 are independently hydrogen, C1-C3 alkyl, trifluoromethyl or halogen; p is an integer of 0 to 6; and s is an integer of 1 to 6.
The present invention further provides an insecticidal/acaricidal agent containing the above dihalopropene compound as an active ingredient.
The present invention further provides the following compounds which are useful as intermediates for producing some of the present compounds:
a phenol compound which is 3,5-dichloro-4-(2-(2-(4-chlorophenyl)-1,3-dioxolan-4yl)ethoxy)phenol;
compounds of the general formula: 
wherein R5, R6 and R7 are independently hydrogen, C1-C3 alkyl or trifluoromethyl; R15 is halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy; R2, R3 and R10 are independently halogen, C1-C3 alkyl or C1-C3 haloalkyl; t is an integer of 0 to 2; u is an integer of 1 to 4; w is an integer of 1 to 4; and B is oxygen, S(O)q or NR9 wherein R9 is hydrogen, acetyl or C1-C3 alkyl and q is an integer of 0 to 2;
compounds of the general formula [I] wherein R5, R6 and R7 are all hydrogen; and R2 and R3 are independently halogen or C1-C3 alkyl; and
2-(3-methanesulfonyloxypropyloxy)-5-trifluoromethylpyridine.
The variables in the above formulae for the present compounds and their intermediates can take the following specific examples.
Examples of the C1-C3 alkyl group represented by R2, R3, R4, R5, R6, R7, R9, R10, R11, R12, R13 or R14 are methyl, ethyl, n-propyl and isopropyl.
Examples of the halogen atom represented by R13 or R14 are fluorine, chlorine, bromine and iodine.
Examples of the heterocyclic ring in the optionally substituted heterocyclic ring group represented by A are isoxazole, isothiazole, thiazole, 1,3,4-thiadiazole, pyrrole, furan, thiophene, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,3,4-tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,2,4-triazine, 1,3,5-triazine, indole, benzofuran, thianaphthalene, indazole, benzimidazole, benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, quinazole, piperidine, piperazine, tetrahydrofuran, tetrahydropyran, pyrazoline, phthalimide, dioxane, dioxolane and benzodioxolane.
Examples of the substituent on the optionally substituted heterocyclic ring group represented by A are those of the general formula: (R8)r (wherein R8 is halogen, nitro, cyano, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C2 alkylsulfinyl, C1-C2 alkylsulfonyl, C1-C2 haloalkylsulfinyl, C1-C2 haloalkylsulfonyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, C3-C6 cycloalkyl, (C1-C2 alkyl)aminocarbonyl or [di(C1-C2 alkyl)amino]carbonyl, or R8 is phenyl, benzyl, phenoxy, benzyloxy or pyridyloxy, each of which is optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy or C1-C3 haloalkoxy; and r is an integer of 0 to 7.
Examples of the halogen atom represented by R8 or present in R8 are fluorine, chlorine, bromine and iodine.
Examples of the C1-C4 alkyl group represented by R8 or present in R8 are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.
Examples of the C1-C3 haloalkyl group represented by R8 or present in R8 are trifluoromethyl, difluoromethyl, bromodifluoromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, 2,2,3,3,3-pentafluoropropyl, 3,3,3-trifluoropropyl, 1-fluoropropyl, 2-chloropropyl and 3-bromopropyl.
Examples of the C1-C4 alkoxy group represented by R8 or present in R8 are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and tert-butoxy.
Examples of the C1-C3 haloalkoxy group represented by R8 or present in R8 are trifluoromethoxy, difluoromethoxy, bromofluoromethoxy, 2-fluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 1,2,2,3,3,3-hexafluoropropoxy, 3-fluoropropoxy, 3-chloropropoxy, 3-bromopropoxy, 2,2,3,3,3-pentafluoropropoxy, 3,3,3-trifluoropropoxy and 1,1,2,2,2-pentafluoroethoxy.
Examples of the C1-C3 alkylthio group represented by R8 are methylthio, ethylthio, n-propylthio and isopropylthio.
Examples of the C1-C3 haloalkylthio group represented by R8 are trifluoromethylthio, difluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, 2-bromo-1,1,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloroethylthio, 2-fluoroethylthio, 2-bromoethylthio, 3-fluoropropylthio, 3-chloropropylthio, (3-bromopropyl)thio, 2,2,3,3,3-pentafluoropropylthio and 3,3,3-trifluoropropylthio.
Examples of the C1-C2 alkylsulfinyl group represented by R8 are methylsulfinyl and ethylsulfinyl.
Examples of the C1-C2 alkylsulfonyl group represented by R8 are methylsulfonyl and ethylsulfonyl.
Examples of the C1-C2 haloalkylsulfinyl group represented by R8 are trifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and perfluoroethylsulfinyl.
Examples of the C1-C2 haloalkylsulfonyl group represented by R8 are trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl and perfluoroethylsulfonyl.
Examples of the C2-C4 alkenyl group represented by R8 are vinyl, isopropenyl, 1-propenyl, 2-ethyl-1-propenyl, 1-methyl-1-propenyl, allyl, 2-methylpropenyl and 2-butenyl.
Examples of the C2-C4 haloalkenyl group represented by R8 are 2,2-dichloroethenyl, 2,2-dibromoethenyl, 3,3-dichloroallyl, 3,3-dibromoallyl, 2,3-dichloroallyl, 2,3-dibromoallyl, 2-chloro-2-propenyl, 3-chloro-2-propenyl, 2-bromo-2-propenyl and 3-chloro-2-butenyl.
Examples of the C2-C4 alkynyl group represented by R8 are ethynyl, 1-propynyl, 2-propynyl and 1-methyl-2-propynyl.
Examples of the C2-C4 haloalkynyl group represented by R8 are chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl, 1-methyl-3-chloro-2-propynyl, 1-methyl-3-bromo-2-propynyl and 1-methyl-3-iodo-2-propynyl.
Examples of the haloacetyl group represented by R8 are trifluoromethylacetyl and trichloroacetyl.
Examples of the C3-C6 cycloalkyl group represented by R8 are cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
Examples of the C5-C6 cycloalkenyl are 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl and 3-cyclohexenyl.
Examples of the (C1-C2 alkyl)aminocarbonyl group represented by R8 are methylaminocarbonyl and ethylamino carbonyl.
Examples of the [di(C1-C2 alkyl)amino]carbonyl group represented by R8 are dimethylaminocarbonyl, N-methyl-N-ethylaminocarbonyl and diethylaminocarbonyl.
The following are preferred examples of the present compound:
dihalopropene compounds wherein A is a 5- or 6-membered heterocyclic ring group containing at least one oxygen, sulfur or nitrogen and optionally substituted by (R8)r (wherein R8 is halogen, nitro, cyano, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C2 alkylsulfinyl, C1-C2 alkylsulfonyl, C1-C2 haloalkylsulfinyl, C1-C2 haloalkylsulfonyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, C3-C6 cycloalkyl, (C1-C2 alkyl)-aminocarbonyl or [di(C1-C2 alkyl)amino]carbonyl, or R8 is phenyl, benzyl, phenoxy, benzyloxy or pyridyloxy, each of which is optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy or C1-C3 haloalkoxy; and r is an integer of 0 to 7);
dihalopropene compounds wherein A is 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 5-(1,3-thiazolyl), N-(1,2-dihydro-2-oxo)pyridino, 1,3-dioxolanyl, 1,4-benzodioxanyl, 2-pyrazyl, 2-benzothiazolyl, 2-benzoxazolyl, 2-benzimidazolyl, 2-quinoxalynyl, N-benzimidazolyl, 2-quinolyl, 3-quinolyl or N-phthalimido, each of which is optionally substituted with (R8)r (wherein R8 and r are each as defined above);
dihalopropene compounds wherein R2 and R3 are independently halogen or C1-C3 alkyl, and t is 0;
dihalopropene compounds wherein R2 and R3 are independently chlorine, bromine, methyl, ethyl or isopropyl, and t is 0;
dihalopropene compounds wherein R2 and R3 are both chlorine, and t is 0;
dihalopropene compounds wherein R2 is chlorine, R3 is methyl, and t is 0;
dihalopropene compounds wherein R2 is ethyl, R3 is methyl, and t is 0;
dihalopropene compounds wherein R2 and R3 are both bromine, and t is 0;
dihalopropene compounds wherein R2 and R3 are both ethyl, and t is 0;
dihalopropene compounds wherein R2 and R3 are independently halogen or C1-C3 alkyl, t is 1 or 2, and R10 is halogen or C1-C3 alkyl;
dihalopropene compounds wherein R2 and R3 are independently halogen or C1-C3 alkyl, t is 1 or 2, and R10 is halogen;
dihalopropene compounds wherein Y and Z are both oxygen;
dihalopropene compounds wherein R2 is Q1, p is 1 to 6, and A is 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 5-(1,3-thiazolyl), N-(1,2-dihydro-2-oxo)pyridino, 1,3-dioxolanyl or N-phthalimido, each of which is optionally substituted with (R8)r (wherein R8 and r are each as defined above);
dihalopropene compounds wherein R1 is Q1, p is 1 to 6, R5, R6 and R7 are all hydrogen, and A is 1,3-dioxolanyl optionally substituted with (R8)r (wherein R8 and r are each as defined above);
dihalopropene compounds wherein R1 is Q1, p is 1 to 4, R5, R6 and R7 are all hydrogen, and A is 1,3-dioxolanyl optionally substituted with (R8)r (wherein R8 and r are each as defined above);
dihalopropene compounds wherein R1 is Q1, p is 0, and A is 2-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 5-(1,3-thiazolyl), 1,3-dioxolanyl or 1,4-benzodioxolanyl, each of which is optionally substituted with (R8)r (wherein R8 and r are each as defined above);
dihalopropene compounds wherein R1 is Q2;
dihalopropene compounds wherein R1 is Q2, and A is 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 5-(1,3-thiazolyl), 2-pyradyl, 2-benzothiazolyl, 2-benzoxazolyl, 2-benzimidazolyl, 2-quinoxalynyl, N-benzimidazolyl, 2-quinolynyl or 3-quinolyl, each of which is optionally substituted with (R8)r (wherein R8 and r are each as defined above);
dihalopropene compounds wherein R1 is Q2, p is 1 to 4, and A is 2-pyridyl optionally substituted with (R8)r (wherein R8 and r are each as defined above);
dihalopropene compounds wherein R1 is Q2, p is 1 to 4, R5, R6 and R7 are all hydrogen, and A is 2-pyridyl optionally substituted with (R8)r (wherein R8 and r are each as defined above);
dihalopropene compounds wherein R1 is Q2, p is 1 to 4, R5, R6 and R7 are all hydrogen, A is 2-pyridyl optionally substituted with (R8)r (wherein R8 is halogen or C1-C3 haloalkyl and r is as defined above);
dihalopropene compounds wherein R1 is Q2, p is 2 or 3, R5, R6 and R7 are all hydrogen, A is 2-pyridyl optionally substituted with (R8)r (wherein R8 is halogen or C1-C3 haloalkyl and r is as defined above);
dihalopropene compounds wherein R1 is Q2, p is 2 or 3, R5, R6 and R7 are all hydrogen, A is 2-pyridyl optionally substituted with (R8)r (wherein R8 is halogen or trifluoromethyl and r is as dined above); and
dihalopropene compounds wherein R1 is Q2, p is 2 or 3, R5, R6 and R7 are all hydrogen, B is oxygen, A is 2-pyridyl optionally substituted with (R8)r (wherein R8 is halogen or trifluoromethyl and r is as defined above).
The following are particularly preferred examples of the present compound. wherein numbers in parentheses are the corresponding compound numbers used below.
(36) 3,5-Dichloro-4-(3-(5-trifluoromethyl-2-pyridyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene;
(47) 3-Ethyl-5-methyl-4-(3-(5-trifluoromethyl-2-pyridyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene; and
(49) 3,5-Dichloro-4-(3-(5-trifluoromethyl-2-pyridylamino)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
The present compounds can be produced, for example, by the following production processes A-H.
(Production Process A)
In this process, a compound of the general formula: 
wherein R1, R2, R3, R10, t, Y and Z are each as defined above, is reacted with a halide compound of the general formula:
xe2x80x83Lxe2x80x94CH2CHxe2x95x90CX2xe2x80x83xe2x80x83[IV]
wherein X is as defined above and L is halogen (e.g., chlorine, bromine, iodine), mesyloxy or tosyloxy.
The reaction is preferably effected in an inert solvent in the presence of a suitable base.
Examples of the solvent that can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C1-C4) ether (e.g., diethyl ether, diisopropyl ether); N,N-di-methylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used.
Examples of the base which can be used are hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., C1-C4), such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. If necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system at a ratio of 0.01 to 1 mole per mole of the compound of the general formula [III].
The reaction temperature is usually set within the range of xe2x88x9220xc2x0 C. to 150xc2x0 C. or the boiling point of a solvent used in the reaction, preferably xe2x88x925xc2x0 C. to 100xc2x0 C. or the boiling point of a solvent used in the reaction.
The molar ratio of the starting materials and bases to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out, if necessary, by an ordinary technique such as chromatography, distillation or recrystallization.
(Production Process B for the present compounds wherein Y is oxygen)
In this process, a compound of the general formula [III] is reacted with an alcohol compound of the general formula:
HOxe2x80x94CH2CHxe2x95x90CX2xe2x80x83xe2x80x83[V]
wherein X is as defined above.
The reaction is preferably effected in an inert solvent, if necessary, in the presence of a suitable dehydrating agent.
Examples of the dehydrating agent which can be used are dicyclohexylcarbodiimide, and dialkyl (e.g., C1-C4) azodicarboxylates (e.g., diethylazodicarboxylate, diisopropylazodicarboxylate)-trialkyl (e.g., C1-C20) phosphine or triarylphosphine (e.g., triphenylphosphine, trioctylphosphine, tributylphosphine).
Examples of the solvent which can be used are hydrocarbons such as benzene, xylene and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene and dichlorobenzene.
The reaction temperature is usually set within the range of xe2x88x9220xc2x0 C. to 200xc2x0 C. or the boiling point of a solvent used in the reaction.
The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.
(Production Process C for the present compounds wherein Y is oxygen)
In this process, an aldehyde compound of the general formula: 
wherein R1, R2, R3, R10, t and Z are each as defined above, is reacted with carbon tetrachloride or carbon tetrabromide.
The reaction is preferably effected in an inert solvent in the presence of a suitable trialkylphosphine or triarylphosphine, and if necessary, in the presence of metal zinc.
Examples of the solvent which can be used are hydrocarbons such as benzene, xylene and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; and halogenated hydrocarbons (exclusive of carbon tetrabromide and carbon tetrachloride) such as dichloromethane, 1,2-dichloroethane and chlorobenzene.
The reaction temperature is usually set within the range of xe2x88x9230xc2x0 C. to 150xc2x0 C. or the boiling point of a solvent used in the reaction.
Examples of the trialkyl (e.g., C1-C20) phosphine or triarylphosphine are triphenylphosphine and trioctylphosphine. The metal zinc which is used, if necessary, is preferably in dust form.
The molar ratio of the starting materials and reagents to be used in the reaction can be freely determined, but the ratio is preferably such that carbon tetrabromide or tetrachloride, trialkylphosphine or triarylphosphine, and zinc are 2 moles, 2 or 4 moles (2 moles when zinc is used), and 2 moles, respectively, per mole of the aldehyde compound of the general formula [VI], or it is favorable to effect the reaction at a ratio closer thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.
(Production Process D for the present compounds wherein Y and Z are both oxygen)
In this process, a compound of the general formula: 
wherein R2, R3, R10, t and X are each as defined above, is reacted with a compound of the general formula:
R1xe2x80x94Lxe2x80x83xe2x80x83[VIII]
wherein R1 and L are each as defined above.
The reaction is preferably effected in an inert solvent in the presence of a suitable base.
Examples of the solvent which can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C1-C4) ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used.
Examples of the base which can be used are hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., C1-C4) such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; organic bases such as triethylamine and pyridine. If necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system at a ratio of 0.01 to 1 mole per mole of the compound of the general formula [VII].
The reaction temperature is usually set within the range of xe2x88x9220xc2x0 C. to 150xc2x0 C. or the boiling point of a solvent used in the reaction, preferably xe2x88x925xc2x0 C. to 100xc2x0 C. or the boiling point of a solvent used in the reaction.
The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.
(Production Process E for the present compounds wherein Y and Z are both oxygen)
In this process, a compound of the general formula [VII] is reacted with an alcohol compound of the general formula:
xe2x80x83R1xe2x80x94OHxe2x80x83xe2x80x83[IX]
wherein R1 is as defined above.
The reaction is preferably effected in an inert solvent, if necessary, in the presence of a suitable dehydrating agent.
Examples of the dehydrating agent which can be used are dicyclohexylcarbodiimide, and dialkyl (e.g., C1-C4) azodicarboxylates (e.g., diethylazodicarboxylate, diisopropylazodicarboxylate)-trialkyl (e.g., C1-C20) phosphine or triarylphosphine (e.g., triphenylphosphine, trioctylphosphine, tributylphosphine).
Examples of the solvent which can be used are hydrocarbons such as benzene, xylene and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene and dichlorobenzene.
The reaction temperature is usually set within the range of xe2x88x9220xc2x0 C. to 200xc2x0 C. or the boiling point of a solvent used in the reaction.
The molar ratio of the materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.
(Production Process F for the present compounds wherein Y and Z are both oxygen, R1 is Q2 or Q3, and B is B1 (wherein B 1 is oxygen, sulfur or NR9 [wherein R9 is as defined above]))
In this process, a compound of the general formula: 
wherein B1, R2, R3, R5, R6, R7, R10, p, t and X are each as defined above, is reacted with a compound of the general formula: 
wherein A, R11, R12, L and s are each as defined above.
The reaction is preferably effected in an inert solvent in the presence of a suitable base.
Examples of the solvent which can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C1-C4) ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used.
Examples of the base which can be used are hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., C1-C4) such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; organic bases such as triethylamine and pyridine. If necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system at a ratio of 0.01 to 1 mole per mole of the compound of the general formula [X].
The reaction temperature is usually set within the range of xe2x88x9220xc2x0 C. to 150xc2x0 C. or the boiling point of a solvent used in the reaction, preferably xe2x88x925xc2x0 C. to 100xc2x0 C. or the boiling point of a solvent used in the reaction.
The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.
(Production Process G for the present compounds wherein Y, Z and B are all oxygen and R1 is Q2, Q3, Q6 or Q7)
In this process, an alcohol compound of the general formula: 
wherein R2, R3, R10, R5, R6, R7, p, t and X are each as defined above, is reacted with compound Q21, Q31, Q61 or Q71 of the general formula: 
wherein R11, R12, R13, R14 A and s are each as defined above.
The reaction is preferably effected in an inert solvent, if necessary, in the presence of a suitable dehydrating agent.
Examples of the dehydrating agent which can be used are dicyclohexylcarbodiimide, and dialkyl (e.g., C1-C4) azodicarboxylates (e.g., diethylazodicarboxylate, diisopropylazodicarboxylate)-trialkyl (e.g., C1-C20) phosphine or triarylphosphine (e.g., triphenylphosphine, trioctylphosphine, tributylphosphine).
Examples of the solvent which can be used are hydrocarbons such as benzene, xylene and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene and dichlorobenzene.
The reaction temperature is usually set within the range of xe2x88x9220xc2x0 C. to 200xc2x0 C. or the boiling point of a solvent used in the reaction.
The molar ratio of the materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.
(Production Process H for the present compounds wherein Y and Z are both oxygen and R1 is Q2, Q3, Q6 or Q7)
In this process, a compound of the general formula: 
wherein R2, R3, R5, R6, R7, R10, X, L, p and t are each as defined above, is reacted with compound Q22, Q32, Q62 or Q72 of the general formula: 
wherein R11, R12, R13, R14, A, B and s are each as defined above.
The reaction is preferably effected in an inert solvent in the presence of a suitable base.
Examples of the solvent which can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C1-C4) ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used.
Examples of the base which can be used are hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., C1-C4) such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; organic bases such as triethylamine and pyridine. If necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system at a ratio of 0.01 to 1 mole per mole of the compound of the general formula [XIV].
The reaction temperature is usually set within the range of xe2x88x9220xc2x0 C. to 150xc2x0 C. or the boiling point of a solvent used in the reaction, preferably xe2x88x925xc2x0 C. to 100xc2x0 C. or the boiling point of a solvent used in the reaction.
The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.
When the present compound has an asymmetry carbon atom, it is to be construed to include its optically active isomers ((+)-form and (xe2x88x92)-form) having biological activity and their mixtures at any ratio. When the present compound exhibits geometrical isomerism, it is to be construed to include its geometrical isomers (cis-form and transform) and their mixtures at any ratio.
The following are typical examples of the present compound (wherein R1 is as shown in Tables 1 to 46), which are not to be construed to limit the scope of the present invention. 
In Tables 31 to 34, (R8)r is defined as followed:
The aldehyde compound of the general formula [VI], which is an intermediate for use in the production of the present compounds, can be produced, for example, according to the following scheme 1: 
wherein all variables are as defined above.
The compounds of the general formula [II] or [III], which are intermediate for use in the production of the present compounds, can be produced, for example, according to the following schemes 2 to 6: 
The compounds of the general formula [VII], which are intermediates for use in the production of the present compounds, can be produced, for example, according to the following scheme 7: 
The compounds of the general formula [IV] and the alcohol compounds of the general formula [V], which are intermediates for use in the production of the present compounds, can be produced, for example, according to the following scheme 8: 
wherein L2 is chlorine or bromine, L3 is mesyloxy or tosyloxy, and X is as defined above.
The compounds of the general formula [VIII] or [IX] wherein R1 is R11 (wherein R11 is Q1 or Q2 in the definition of R1), which are intermediates for use in the production of the present compounds, can be obtained from various commercial sources or can be produced, for example, according to the schemes 9 and 10 depicted below.
The aldehyde compounds of the general formula: Axe2x80x94CHO (wherein A is as defined above), which are the starting compounds in the production of the compounds [VIII] or [IX], can be obtained, for example, by the processes disclosed in the following references.
Furancarbaldehydes:
Zh. Org. Khim., 11, 1955;
Tetrahedron., 39, 3881;
Chem. Pharm. Bull., 28, 2846
Thiophenecarbaldehydes:
Tetrahedron., 32, 1403;
J. Org. Chem., 41, 2835;
Zh. Obshch. Khim., 34, 4010;
Bull. Soc. Chim. France., 479 (1963)
Pyrrolecarbaldehydes:
Beilstein., 21, 1279
Isothiazolecarbaldehydes:
J. Medicin. Chem., 13, 1208;
J. Chem. Soc., 446 (1964)
Pyrazolecarboaldehydes:
Chem. Ber., 97, 3407;
J. Chem. Soc., 3314 (1957)
Imidazolecarbaldehydes:
J. Pharm. Soc. Japan., 60, 184;
J. Amer. Chem. Soc., 71, 2444
Thiazolecarbaldehydes:
JP-A 59-206370/1984
Chem. Ab., 62, 7764d;
Chem. Ber., 101, 3872;
JP-A 59-206370/1984
Thiadiazolecarbaldehydes:
U.S. Pat. No. 1,113,705 
wherein all the variables are each as defined above. 
wherein all the variables are each as defined above.
The compounds of the general formula: A-Lxe2x80x2 (wherein Lxe2x80x2 is halogen (e.g., chlorine, bromine, iodine)) included in the compounds [XI], which are intermediates for use in the production of the present compounds, can be obtained from various commercial sources or can be produced, for example, according to the following scheme 11: 
wherein A and Lxe2x80x2 are each as defined above.
The compounds [X], [XII] or [XIII], which are intermediates for use in the production of the present compounds, can be produced, for example, according to the following schemes 12 and 13: 
wherein all the variables are each as defined above.
*) J.Amer.Chem.Soc., 33, 440 (1905) 
wherein MS is mesyl; TS is tosyl; R16 is a protecting group for alcohols (e.g., benzoyl); R17 is protected formyl (e.g., acetal); L1 is hydroxy or L; and R2, R3, R7, R10, R11, R14, X, L, p and t are each as defined above. 
wherein all the variables are each as defined above.
The present compounds are satisfactorily effective for the control of various noxious insects, mites and ticks, examples of which are as follows:
Hemiptera
Delphacidae such as Laodelphax striatellus, Nilaparvata lugens and Sogatella furcifera, Deltocephalidae such as Nephotettix cincticeps and Nephotettix virescens, Aphididae, Pentatotnidae, Aleyrodidae , Coccidae, Tin gidae, Psyllidae, etc.
Lepidoptera
Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinialis, Ostrinia nubilalis, Parapediasia teterrella, Notarcha derogata and Plodia interpunctella, Noctuidae such as Spodoptera litura, Spodoptera exigua, Spodoptera littoralis, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Trichoplusia spp., Heliothisspp., Helicoverpa spp. and Earias spp., Pieridae such as Pieris rapae crucivora, Tortricidae such as Adoxophyes spp., Grapholita molesta and Cydia pomonella, Carposinidae such as Carposinia niponensis, Lyonetiidae such as Lyonetin spp., Lymantriidae such as Lymantria spp. and Euproctis spp., Yponomeutidae such as Plutella xylostella, Gelechiidae such as Pectinophora gossypiella, Arctiidae such as Hyphantria cunen, Tineidae such as Tinea translucens and Tineola bisselliella, etc.
Diptera
Culex such as Culex pipiens pallens and Cules tritaeniorhynchus, Aedes such as Aedes albopictus and Aedes aegypti, Anopheles such as Anophelinae sinensis, Chironomidae, Muscidae such as Musca domestica and Muscina stabulans, Calliphoridae, Sarcophagidae, Fannia canicularis, Anthomyiidae such as Delia Platura and Delia antigua, Trypetidae, Drosophilidae, Psycllodidae, Tabanidae, Simuliidae, Stomoxyinae, etc.
Coleoptera
Diabrotica such as Diabrotica virgifera and Diabrotica undecimpunctata, Scarabaeidae such as Anomala cuprea and Anomala rufocuprea, Curculionidae such as Lissorphoptrus oryzophilus, Hypera pastica, and Calosobruchys chinensis, Tenebrionidae such as Tenebrio molitor and Tribolium castaneum, Chrysomelidae such as Phyllotreta striolata and Aulacophora femoralis, Anobiidae, Epilachna spp. such as Henosepilachna vigintioctopunctata, Lyctidae, Bostrychidae, Cerambycidae, Paederus fuscipes, etc.
Dictyoptera
Blattella germanica, Periplaneta fuliginosa, Peroplaneta americania, Periplaneta bnrnnea, Blatta orien talis, etc.
Thysanoptera
Thrips palmi, Thrips hawaiiensis, etc.
Hymenoptera
Formicidae, Vespidae, Bethylidae, Tenthredinidae such as Athalia rosae japonensis, etc.
Orthoptera
Gryllotalpidae, Acrididae, etc.
Siphonaptera
Purex irritans, etc.
Anoplura
Pedicuilus humanus capitis, Phthirus pubis, etc.
Isoptera (termites)
Reticulitermes speratus, Coptotermes formnosatitts, etc.
Acarina
plant patasitic Tetran)chidae such as Tetranychus uriticae, Panonychus citri, Tetranychus cinnabarinus and Panonychus ulmi, animal parasitic Ixodidae such as Boophilus microphis, house dust mites, etc.
The present compounds are also effective for the control of various noxious insects, mites and ticks having resistance to conventional insecticides and acaricides.
When the present compound is used as an active ingredient of insecticidal/acaricidal agents, it may be used as such without any addition of other ingredients. The present compound is, however, usually formulated into a dosage form such as oil sprays, emulsifiable concentrates, wettable powders, flowables, granules, dusts, aerosols, fumigants (foggings) and poison baits. These formulations are usually prepared by mixing the present compound with a solid carrier, a liquid carrier, a gaseous carrier or a bait, and if necessary, adding a surfactant and other auxiliaries used for formulation.
Each of the formulations usually contains the present compound as an active ingredient in an amount of 0.01% to 95% by weight.
Examples of the solid carrier to be used for the formulation are fine powder or granules of clay materials such as kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, Fubasami clay and acid clay; various kinds of talc, ceramics, other inorganic minerals such as sericite, quartz, sulfur, active carbon, calcium carbonate and hydrated silica; and chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride.
Examples of the liquid carrier are water; alcohols such as methanol and ethanol; ketones such as acetone and methyl ethyl ketone; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene and methylnaphthalene; aliphatic hydrocarbons such as hexane, cyclohexane, kerosine and gas oil; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and isobutyronitrile; ethers such as diisopropyl ether and dioxane; acid amides such as N,N-dimethylformamide and N,N-dimethylacetamide; halogenated hydrocarbons such as dichloromethane, trichloroethane and carbon tetrachloride; dimethyl sulfoxide; and vegetable oils such as soybean oil and cottonseed oil.
Examples of the gaseous carrier or propellant are flon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.
Examples of the surfactant are alkyl sulfates, alkyl sulfonates, alkyl arylsulfonates, alkyl aryl ethers and their polyoxyethylene derivatives, polyethylene glycol ethers, polyhydric alcohol esters and sugar alcohol derivatives.
Examples of the auxiliaries used for formulation, such as fixing agents or dispersing agents, are casein, gelatin, polysaccharides such as starch, gum arabic, cellulose derivatives and alginic acid, lignin derivatives, bentonite, sugars, and synthetic water-soluble polymers such as polyvinyl alcohol, polyvinyl pyrrolidone and polyacrylic acid.
Examples of the stabilizer are PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (mixtures of 2-t-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, surfactants, fatty acids and their esters.
Examples of the base material to be used in the poison baits are bait materials such as grain powder, vegetable oils, sugars and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; preservatives such as dehydroacetic acid; substances for preventing erroneous eating, such as red pepper powder, attractant flavors such as cheese flavor or onion flavor.
The formulation thus obtained is used as such or after diluted with water. The formulation may also be used in combination with other insecticides, nematocides, acaricides, bactericides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners and/or animal feed under non-mixing conditions or premixing conditions.
Examples of the insecticide, acaricide and/or nematocide which can be used are organophosphorus compounds such as Fenitrothion [(O,O-dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioate], Fenthion [O,O-dimethyl O-(3-methyl-4-methylthio)phenyl)phophorothioate], Diazinon [O,O-diethyl-O-2-isopropyl-6-methylpyrimidin-4-ylphosphorothioate], Chlorpyriphos [O,O-diethyl-O-3,5,6-trichloro-2-pyridylphosphorothioate], Acephate [O,S-dimethylacetylphosphoramidothioate], Methidachion [S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethylphosphorodithioate], Disulfoton [O,O-diethyl S-2-ethylthioethylphosphorothioate], DDVP [2,2-dichlorovinyldimethylphosphate], Sulprofos [O-ethyl O-4-(methylthio)phenyl S-propyl phosphorodithioate], Cyanophos [O-4-cyanophenyl O,O-dimethylphosphorothioate], Dioxabenzofos [2-methoxy-4H-1,3,2-benzodioxaphosphinin-2-sulfide], Dimethoate [O,O-dimethyl-S-(N-methylcarbamoylmethyl)dithiophosphate], Phenthoate [ethyl 2-dimethoxyphosphinothioylthio(phenyl)acetate], Malathion [diethyl(dimethoxyphosphinothioylthio)succinate], Trichlorfon [dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate], Azinphos-methyl [S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl-O,O-dimethylphosphorodithioate], Monocrotophos [dimethyl (E)-1-methyl-2-(methylcarbamoyl)vinylphosphate], Ethion [O,O,Oxe2x80x2,Oxe2x80x2-tetraethyl S,Sxe2x80x2-methylenebis(phosphorodithioate)] and Profenfos [O-4-bromo-2-chlorophenyl O-ethyl S-propylphosphorothioate]; carbamate compounds such as BPMC [2-secbutylphenylmethylcarbamate], Benfuracarb [ethyl N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-xcex2-alaninate], Propoxur [2-isopropoxyphenyl N-methylcarbamate], Carbosulfan [2,3-dihydro-2,2-dimethyl-7-benzo[b]-furanyl N-dibutylaminothio-N-methylcarbamate], Carbaril [1-naphthyl-N-methylcarbamate], Methomyl [S-methyl-N-[(methylcarbamoyl)oxy]thioacetoimidate], Ethiofencarb [2-(ethylthiomethyl)phenylmethylcarbamate], Aldicarb [2-methyl-2-(methylthio)propanaldehyde O-methylcarbamoyloxime], Oxamyl [N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide], Alanylcarb [ethyl (Z)-N-benzyl-N-{[methyl(1-methylthioethylideneaminooxycarbonyl)amino]thio}-xcex2-alanylate], Fenothiocarb [S-(4-phenoxybutyl)-N,N-dimethylthiocarbamate] and Thiodicarb [3,7,9,13-tetramethyl-5,11-dioxa-2,8,14-trithia-4,7,9,12-tetraazapentadeca-3,12-dien-6,10-dione]; pyrethroid compounds such as Etofenprox [2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzylether], Fenvalerate [(RS)-xcex1-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate], Esfenvalerate [(S)-xcex1-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate], Fenpropathrin [(RS)-xcex1-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], Cypermethrin [(RS)-xcex1-cyano-3-phenoxybenzyl (1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Permethrin [3-phenoxybenzyl (1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Cyhalothrin [(RS)-xcex1-cyano-3-phenoxybenzyl (Z)-(1RS,3RS)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate], Deltamethrin [(S)-xcex1-cyano-m-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate], Cycloprothrin [(RS)-xcex1-cyano-3-phenoxybenzyl (RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate], Fluvalinate [xcex1-cyano-3-phenoxybenzyl N-(2-chloro-xcex1,xcex1,xcex1-trifluoro-p-tolyl)-D-valinate], Bifenthrin [2-methylbiphenyl-3-ylmethyl)(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoropropen-1-yl)-2,2-dimethylcyclopropanecarboxylate], Acrinathrin [cyano-(3-phenoxyphenyl)methyl [1R-{1xcex1(S*),3xcex1(Z)}]-2,2-diethyl-3-[3-oxo-3-(2,2,2-trifluoro-1-(trifluoromethyl)ethoxy-1-propenyl]cyclopropanecarboxylate], 2-methyl-2-(4-bromodifluoromethoxyphenyl)propyl (3-phenoxybenzyl) ether, Traromethrin [(S)-xcex1-cyano-3-phenoxylbenzyl (1R, 3R)-3-[(1xe2x80x2RS)(1xe2x80x2,1xe2x80x2,2xe2x80x2,2xe2x80x2-tetrabromoethyl)]-2,2-dimethylcyclopropanecarboxylate] and Silafluofen [4-ethoxylphenyl [3-(4-fluoro-3-phenoxyphenyl)propyl]dimethylsilane]; thiadiazine derivatives such as Buprofezin [2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazin-4-one]; nitroimidazolidine derivatives such as Imidacloprid [1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylidenamine]; Nereistoxin derivatives such as Cartap [S,S xe2x80x2-(2-dimethylaminotrimethylene)bisthiocarbamate], Thiocyclam [N,N-di-methyl-1,2,3-trithian-5-ylamine] and Bensultap [S,Sxe2x80x2-2-dimethylaminotrimethylene di-(benzenethiosulfonate)]; N-cyanoarmidine derivatives such as acetamiprid [N-cyano-Nxe2x80x2-methyl-Nxe2x80x2-(6-chloro-3-pyridylmethyl)acetamidine]; chlorinated hydrocarbons such as Endosulfan [6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepinoxide], xcex3-BHC [1,2,3,4,5,6-hexachlorocyclohexane] and Kelthane [1,1-bis(chlorophenyl)-2,2,2-trichloroethanol]; benzoylphenylurea compounds such as Chlorfluazuron [1-(3,5-dichloro-4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl)-3-(2,6-difluorobenzoyl)urea], Teflubenzuron [1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea] and Fulphenoxron [1-(4-(2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl)-3-(2,6-difluorobenzoyl)urea]; formamidine derivatives such as Amitraz [N,Nxe2x80x2-[(methylimino)dimethylidine]-di-2,4-xylidine] and Chlordimeform [Nxe2x80x2-(4-chloro-2-methylphenyl)-N,N-dimethylmethanimidamide]; thiourea derivatives such as Diafenthiuron [N-(2,6-diisopropyl-4-phenoxyphenyl)-Nxe2x80x2-tert-butylcarbodiimide]; Fipronyl [5-amino-1-(2,6-dichloro-xcex1,xcex1,xcex1-trifluoro-p-tolyl)-4-trifluoromet hylsulfinylpyrazole-3-carbonitrite], Tebfenozide [N-tert-butyl-Nxe2x80x2-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide], 4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrole-3-carbonitrile, Chlorfenapyl [4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-S-trifluoromethylpyrole-3-carbonitril], Bromopropylate [isopropyl 4,4xe2x80x2-dibromobenzylate], Tetradifon [4-chlorophenyl-2,4,5-trichlorophenyl sulfone], Quinomethionate [S,S-6-methylquinoxaline-2,3-diyldithiocarbonate], Propargite [2-(4-tert-butylphenoxy)cyclohexyl prop-2-yl sulfite], Fenbutatin oxide [bis[tris(2-methyl-2-phenylpropyl)tin)oxide], Hexythiazox [(4RS,5RS)-5-(4-chlorophenyl)-N-chlorohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide], Chlofentezine [3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine], Pyridaben [2-tert-butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one], Fenpyroximate [tert-butyl-(E)-4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxymethyl]benzoate], Tebfenpyrad [N-4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazol carboxamide], polynactin complexes including tetranactin, dinactin and trinactin; Milbemectin, Avermectin, Ivermectin, Azadilactin [AZAD], Pyrimidifen [5-chloro-N-[2-{4-(2-ethoxyethyl)-2,3-dimethylphenoxy}ethyl]-6-ethylpyrimidin-4-amine] and Pimetrozine [2,3,4,5-tetrahydro-3-oxo-4-[(pyridin-3-yl)-methyleneatnino]-6-methyl-1,2,4-triazine].
When the present compound is used as an active ingredient of insecticidal/acaricidal agents for agriculture, the application amount thereof is usually in the range of 0.1 to 100 g per 10 ares. In the case of emulsifiable concentrates, wettable powders and flowable concentrates, which are used after diluted with water, the application concentration thereof is usually in the range of 0.1 to 500 ppm. In the case of granules and dusts, they are applied as such without any dilution. When the present compound is used as an active ingredient of insecticidal/acaricidal agents for epidemic prevention, it is formulated into a dosage form such as emulsifiable concentrates, wettable powders and flowable concentrates, which are applied after diluted with water to a typical concentration of 0.1 to 500 ppm; or it is formulated into a dosage form such as oil sprays, aerosols, fumigants and poisonous baits, which are applied as such without any dilution.
The application amount and application concentration may vary depending upon various conditions such as formulation type, application time, place and method, kind of noxious insects, mites and ticks, and degree of damage, and they can be increased or decreased without limitation to the above range.
The present invention will be further illustrated by the following production examples, formulation examples and test examples, which are not to be construed to limit the scope thereof.
The following are production examples for the present compounds according to various production processes.